Tetrahydrofuran → (4-Benzyloxy-phenyl)(6-ethynylquinazolin-4-yl)-amine

HRID 1936767Notes

Reaction equation

HRID 1936767 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[C:27][Si](C)(C)C)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[CH:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 22609859(4-Benzyloxy-phenyl)-(6-(trimethylsilylethynyl)quinazolin-4-yl)-amine

Product 1

HCID 22609768(4-Benzyloxy-phenyl)(6-ethynylquinazolin-4-yl)-amineYield 80%

Procedure

The (4-benzyloxy-phenyl)-(6-(trimethylsilylethynyl)quinazolin-4-yl)-amine (0.65 g, 1.53 mmol) was reacted with tetrabutylammonium fluoride in tetrahydrofuran (1.0M, 5.0 ml, 5.0 mmol) at room temperature for 20 min. The solvent was removed in vacuo, and the residual oil was partitioned between water (20 ml) and ethyl acetate (20 ml). After separation, the aqueous was extracted with further ethyl acetate (2×20 ml). The combined organic solutions were dried (Na2SO4) and concentrated in vacuo to give the title compound as an off-white solid (0.43 g, 1.22 mmol, 80%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residual oil was partitioned between water (20 ml) and ethyl acetate (20 ml)
  3. customAfter separation
  4. extractionthe aqueous was extracted with further ethyl acetate (2×20 ml)
  5. dry with materialThe combined organic solutions were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-913c7ff1aff44b79911817916282eed8
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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